HCID 15462733, compound → HCID 15462734, compound

HRID 2229418Notes

Reaction equation

HRID 2229418 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[O:24][CH:23]=[N:22][CH:21]=3)=[C:16]([O:25][CH3:26])[CH:15]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O>O1CCOCC1.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[O:24][CH:23]=[N:22][CH:21]=3)=[C:16]([O:25][CH3:26])[CH:15]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 15462733HCID 15462733, compound

Product 1

HCID 15462734HCID 15462734, compoundYield 46.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.7 g (2 mmol) of 49A in 60 ml of dioxane and 30 ml of methanol was hydrogenated at rt and one atmosphere pressure over 0.14 g of 10% Pd/C catalyst. The catalyst was removed by filtration through Celite. The filtrate was evaporated to dryness to yield 0.3 g of 49B as a tan solid. The filter cake was suspended in dioxane—methanol and stirred at 50° C. for 1 hr. The hot solution was again filtered, and the filtrate evaporated to dryness to yield an additional 0.6 g of material. The combined batches were triturated with methylene chloride and the insolubles filtered to give 645 mg (2 mmoles, 100%) of 49B as a light tan powder.

Workup

  1. customwas hydrogenated at rt
  2. customThe catalyst was removed by filtration through Celite
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-b86e69e80e67424eb795b527b7c64dbd
Source dataset
uspto-grants-2002_07
Patent number
US06420403B1

Reaction notes

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